PMID: 8956082Nov 1, 1996Paper

Solid-phase synthesis of peptide-4-nitroanilides

International Journal of Peptide and Protein Research
A KaspariM Schutkowski

Abstract

A wide variety of Glu/Asp and Gln containing peptide-4-nitroanilides and other chromogenic peptidyl-arylamides could be quickly synthesized by a Fmoc-based solid-phase synthesis strategy employing the side-chain carboxyl groups for transient anchoring to the resin. Suitable synthons for this method, Fmoc-Glu-NH-Np and Fmoc-Asp-NH-Np, were prepared using a diphenylphosphinic chloride-mediated coupling reaction. Peptides of the common structure Suc-Ala-Phe-Pro-Xaa-NH-Np (Xaa = Glu/Asp, Gln) were synthesized and were shown to be substrates for the protease subtilisin Carlsberg (E.C.3.4.21.14a) and for peptidyl-prolyl cis/trans-isomerases (PPIases E.C. 5.2.1.8.). The method was extended to amino acids possessing a side chain missing an anchor for binding to the matrix. We synthesized Suc-Ala-Phe-Pro-Gln-Phe-NH-Np anchoring the dipeptide derivative Fmoc-Glu-Phe-NH-Np with the carboxyl group to Rink amide resin using standard SPPS procedures. Additionally this procedure allowed us the preparation of peptidyl-arylamides, utilizing the commercial available Fmoc-Glu-OAll as building block. A mixture of pentapeptide-4-nitroanilides with the general sequence Ala-Ala-Xaa-Pro-Gln-NH-Np was synthesized. Electrospray ionization mass spectrome...Continue Reading

References

Feb 1, 1990·International Journal of Peptide and Protein Research·F S TjoengS P Adams
Mar 1, 1990·International Journal of Peptide and Protein Research·G BreipohlW Stüber
Apr 1, 1969·Biochemistry·C L Krumdieck, C M Baugh
Dec 1, 1970·The Journal of Organic Chemistry·J MeienhoferI H Rosenberg
Mar 1, 1995·International Journal of Peptide and Protein Research·M SchutkowskiK Neubert
Jan 1, 1994·International Journal of Peptide and Protein Research·L A Reiter
Oct 1, 1993·International Journal of Peptide and Protein Research·A Loffet, H X Zhang

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Citations

Apr 29, 2014·Amino Acids·Prabhakar CherkupallyFernando Albericio
Aug 1, 1997·The Journal of Peptide Research : Official Journal of the American Peptide Society·A BernhardtM Schutkowski
Oct 1, 2003·Biopolymers·Jordi Alsina, Fernando Albericio
Sep 14, 2004·The Biochemical Journal·Hannelore PetersVerena Gauss-Müller
Oct 8, 2004·Organic Letters·Youngeun KwonJulio A Camarero

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